At the trial, the Public Prosecutor, Mr Francis Seow, said that Dutton had died a terrible death, ‘having blundered by under-estimating the size of the uprising’. Mr Seow reckoned that ‘quite a sizeable section’ of the 316 detainees on the island that day were involved in the rioting. He said that trouble had begun when 13 carpenters were sent back to Changi Jail on 9th July for refusing to work on the 400-foot jetty on a Saturday afternoon. Major James later told Dutton that he had been ill-advised to do this.
But even before Dutton had sent the carpenters back, some of the detainees were already plotting to kill him. Informers reported this to Dutton. On 10 July, some of the leaders of the riot drew up a death-list of six prison officers. This list was later amended to include known, or suspected, informers. Men were allocated their respective responsibilities in the uprising. Dutton heard about this the same day. He refused to treat the threat seriously. One of the detainees, the informers said, boasted that the riot would shake the whole of Malaysia (of which Singapore was then part). Dutton was given the latest intelligence reports and also informed about the plot to kill him. Dutton brushed them aside: he preferred to believe that the majority of the detainees would stand by him if there was trouble.
James did not share his optimism. To start with, the Director of Prisons doubted whether any long-time secret society gangster could ever be rehabilitated. He had also opposed the appointment of ex-Pulau Senang detainees as settlement attendants. In his opinion, to employ ex-prisoners in a position of authority in a prison system was wrong. It was quite possible that a detainee could find that he was being supervised by a settlement attendant who was, or had been, a member of a rival secret society. Dutton on the other hand sincerely believed that a man’s salvation came through hard work. He was anxious to retain the services of freed detainees on Pulau Senang who had showed peculiar talents for building, laying pipes, and so on. Dutton had argued that detainees set free would be grateful to be given a ‘government job’ on the island, and would never again turn to a secret society. James, a most experienced prison officer, disagreed. He later told the Court that he thought that ‘government circles’ agreed with him, but he added, ‘certain people’ in the end decided that ex-detainees could be employed as settlement attendants. He felt it to be a mistake.
At the time of the riot, there was a staff of 45 on the island. There were no firearms, no tear gas. There were wicker-shields and batons. In Court, at the trial, James gave his opinion that had Dutton been surrounded by regular prison staff, ‘we might have seen some of the rioters injured. I saw none.’ He added: “If you want my opinion I should say that the staff might well have given a better account of themselves.”
Major James told the Court that it was his decision that there should be no firearms on the island. “We were always out-numbered: if we had firearms there was always a real danger of these arms being taken from us, falling into the hands of the detainees.” The whole question had been discussed at great length with the police. There were no firearms in British prisons. It would have been psychologically wrong for prison staff to walk about Pulau Senang with firearms. “It was our intention to have firearms on the neighbouring island of Pulau Pawai where we were building an armoury. In the event of trouble the orders were to evacuate to this island. The armoury had not been completed by 12 July.” James was asked whether it wouldn’t have been a good idea to have smuggled a Sten-gun into Pulau Senang and hidden it somewhere where Dutton could have had ready access to it. James opposed the idea.
“Would a Sten-gun in that radio room at 1:00 PM on the 12th of July have saved the situation?” asked Mr C.H. Koh, one of the counsel for the defence.
Major James said, “That is debatable.”
Because of what James considered to be Dutton’s misplaced trust in the detainees, he decided to go over to Pulau Senang on 11 July (the day before the uprising) to tell Dutton to take seriously the reports of the plot to kill him, and to take precautions. That was when he told Dutton that he had been ill-advised to send the carpenters back to Changi. James told Dutton that he did not think the work on the jetty was urgent enough to insist upon work on Saturday afternoons. James told Dutton that he would probably send them back again to Pulau Senang within a reasonably short space of time.
The jetty was 400 feet long, and, as Major James explained during the trial, it was necessary to work on it at various odd hours because there is a straits between Pulau Senang and the neighbouring island of Pulau Pawai. There is an extremely strong tide between the two islands, and in building the jetty, Dutton was dependent entirely on the state of the tide. With improvised equipment, the men could only work at low tide. If the tide was low at night, they would work at night. It was not work that could be done at regular working hours. Work depended entirely on tide. Besides, Dutton believed in work.
James felt that Pulau Senang had reached the stage when the detainees had the best amenities that he had ever seen in any prison anywhere, and in 21 years of service, he had been to many prisons in various parts of the world. They had cinema, educational facilities, recreational facilities, good accommodation, laundry, workshops and canteen. James felt that the need for long working hours was over. The original enthusiasm for building could not be the same: the men could no longer see any reason for long working hours.
Dutton thought otherwise. Pulau Senang was not built to be enjoyed. That was not the purpose of the open-prison settlement. Dutton believed fervently that the men’s salvation was hard work.
A defence counsel got Major James to admit that he had ordered Dutton to reduce the working hours. The detainees knew this (there were few secrets on the island). The defence counsel asked James whether Dutton was setting a proper example to those he was trying to teach to respect law and order when Dutton himself disregarded orders. James denied the suggestion that Dutton flagrantly disobeyed orders. He had given Dutton considerable discretion. Dutton was the man on the spot. Pulau Senang was a place where time and tide waited for no man. Things had to be done. Chickens had to be fed, emergency work done. But the type of man on Pulau Senang was a man not liking work. Many people were in prison because they were lazy. Some joined secret societies because they were lazy. James said that no detainee had ever protested or complained to him about working hours, and every prisoner knew he had the right to approach the Director of Prisons with serious complaints.
At 11:30 AM on 12 July, the detainees stopped for lunch. Shortly after the start-work gong struck at 12:40 PM, they were mustered for gardening and issued with cangkuls and parangs. On an arranged signal, the riot began. Some of the rioters attacked the warders. Others made for the radio room where Dutton and his chief officer, J.W. Tailford, had stationed themselves. By now, the warning siren was blaring. By the time the riot squad arrived, inside the hour, Dutton and two others were dead and a third fatally injured. The settlement was in ruins. The final drama had come when the rioters beseiged the administrative block, the settlement’s nerve centre. Outnumbered, the prison staff were overwhelmed. Soon buildings were ablaze. Dutton, seriously injured, alone and helpless, was cornered in his office. Rioters tore a hole in the roof and poured petrol on him and tossed in fire to set him alight. Dutton rushed outside, his clothing in flames, and four rioters with axes and cangkuls finished him off. A rioter’s shirt, stained with Dutton’s blood, was set up on the mast, and as the body of Dutton burned, the rioters played music on a guitar and sang and danced.